Is there any actual synergy at all with the rest of Conde Nast? Would it make sense for Reddit to work with some P.E. people to buy themselves out, and make a venture investment in improving the site?
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Why would anyone make a venture investment in some guys who just admitted that they can't think of how to make money on 280M uniques?
Reddit was (perhaps not intentionally) built to flip. Mission accomplished.
Invest in the 280M uniques, not in the guys.
Put the "Francis M. H. White of Monetization" in as CEO, let the founders be involved in other roles (they're great at building a community and at "ghetto" engineering).
That it is weak sauce now just means you could buy it cheaper. If I had $5-10mm (+100% debt) sitting around and nothing better to do with my life for 2-4 years, I'd be seriously tempted to make an offer to Conde Nast.